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J Am Chem Soc. 2005 Dec 28;127(51):18006-7.

Air-assisted addition of grignard reagents to olefins. A simple protocol for a three-component coupling process yielding alcohols.

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1
Department of Biomolecular Engineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B-59 Nagatsuta-cho, Yokohama, Kanagawa 226-8501, Japan.

Abstract

Silylmethyl, tertiary-alkyl, alkenyl, and aryl Grignard reagents underwent intermolecular addition to olefins, such as styrenes, conjugated dienes, and enynes under an air atmosphere to give homologated alcohols. For example, (trimethylsilyl)methylmagnesium chloride and alpha-methylstyrene in ether at room temperature under dry air directly furnished 2-phenyl-4-(trimethylsilyl)-2-butanol in good yield. As the Grignard addition to olefins under argon with rigorous exclusion of O2 did not proceed at all, the above reaction should involve a radical mechanism: an alkyl radical generated by the aerial oxidation of the Grignard reagent adds to olefin, which is followed by oxygenation. Representative examples of this transformation, where products were obtained in good to excellent diastereo- or regioselectivity, are also disclosed.

PMID:
16366543
DOI:
10.1021/ja055732b
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